RIP: The Hardest-Working Woman At Playboy

Women who work for Playboy are not exactly known for their long shelf life: Hotties at 21 are notties by 30 in the men’s magazine’s oh-so-enlightened view. That’s what makes Mary O’Connor‘s career so fascinating. She was the one woman Hugh Hefner kept around for decade after decade, until death. Nope, not his wife. His secretary.

According to this charming profile in an Irish newspaper, O’Connor was born in Chicago and married a man 11 years her senior when she was 18. She went on to marry four more times, divorcing the first four men before meeting her apparent soul mate, known as Captain Bob.

O’Connor worked for Hefner for more than 40 years. She was a former car-racing promoter, and she ran the original Playboy Mansion in Chicago when it included a dorm for the women who worked in Hefner’s nightclub. The New York Timesreported in 2011 that her more recent duties included buying the fabric for Hef’s pajamas, making his doctor’s appointments, and tending the mansion’s guest list. “You’d think that the well would run dry — the number of people willing to expose themselves by becoming Playmates,” she told Charles McGrath. “But it doesn’t. It just keeps flowing.” She also helped pick out the furniture for the Los Angeles Playboy mansion.

Later in her life, O’Connor was known for her appearances on The Girls Next Door, the E! reality show that focused on the mansion and made stars of Kendra Wilkinson and Holly Madison. Wilkinson tweeted, “She was an amazing person who helped me so much,” and Madison, too, tweeted condolences.

She died Sunday, and Hefner, 86, tweeted his feelings: “Mary passed away today. We loved her more than words can say.” Various articles since 2010 have said that O’Connor was 82. It’s probably safe to assume she was in her 80s, and maybe it’s fitting that a Playboy career woman was a bit shy about aging.